Novel stereoselective synthesis of 1,2,3-trisubstituted azetidines

Tetrahedron Asymmetry

Volumn 23, Issue 22-23, 2012, Pages 1607-1614

  Faigl, Ferenc ^a   Kovács, Ervin ^a   Turczel, Gábor ^a   Szöllsy, Áron ^b   Mordini, Alessandro ^c   Balázs, László ^b   Holczbauer, Tamás ^a   Czugler, Mátyás ^a  

^a INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

^b BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^c UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

3 (1 HYDROXY 2 TRITYLOXYETHYL) 2 PHENYL 1 METHYLAZETIDINE; AZETIDINE DERIVATIVE; TRANS 1 (1 HYDROXY 2 TRITYLOXYETHYL) 2,4,5,9B TETRAHYDRO 1H AZETO[2,1 A]IZOQUINOLINE; TRANS 1 BENZYL 3 (1 HYDROXY 2 TRITYLOXYETHYL) 2 PHENYLAZETIDINE; TRANS 1 ETHYL 2 PHENYL 3 (1 HYDROXY 2 TRITYLOXYETHYL) AZETIDINE; TRANS 1 METHYL 2 PHENYL 3 [1 (TRIMETHYLSILYLOXY) 2 (TRITYLOXY)ETHYL]AZETIDINE; TRANS 1 TERT BUTOXYCARBONYL 3 (1 HYDROXY 2 TRITYLOXYETHYL) 2 PHENYLAZETIDINE; TRANS 3 (1 HYDROXY 2 TRITYLOXYETHYL) 1 METHYL 2 VINYLAZETIDINE; TRANS 3 (1 HYDROXY 2 TRITYLOXYETHYL) 2 PHENYL 1 METHYLAZETIDINE; TRANS 3 (1 HYDROXYBUTYL) 1 METHYL 2 PHENYLAZETIDINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; NUCLEOPHILICITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 84870259465     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2012.10.014     Document Type: Article

References (27)

1. G.B. Evans, R.H. Fumeaux, B. Greatrex, A.S. Murkin, V.L. Schramm, and P.C. Tyler J. Med. Chem. 51 2008 948 956.
2. D. Honcharenko, J. Barman, O.P. Varghese, and J. Chattopadhyaya Biochemistry 46 2007 5635 5646.
3. L. Provins, B. Christophe, P. Danhaive, J. Dulieu, M. Gillard, L. Quere, and K. Stebbins Bioorg. Med. Chem. Lett. 17 2007 3077 3080.
4. L. Kværno, M. Werder, H. Hauser, and E.M. Carreira J. Med. Chem. 48 2005 6035 6053.
5. U.S. 4622327 Patent (1984, CAN 103:160406).
6. U.S. 4713386 Patent (1986, CAN 109:22850).
7. J. Ji, W.H. Bunnelle, T. Li, J.M. Pace, M.R. Schrimpf, K.B. Sippy, D.J. Anderson, and M.D. Meyer Pure Appl. Chem. 77 2005 2041 2045.
8. Y.H. Lee, H.H. Kim, P. Thuéry, J.M. Harrowfield, W.T. Lim, B.J. Kim, and Y. Kim J. Inclusion Phenom. Macrocyclic Chem. 65 2009 65 71.
9. D.-H. Lee, Y.H. Lee, D.I. Kim, Y. Kim, W.T. Lim, J.M. Harrowfield, P. Thuéry, M.-J. Kim, Y.C. Park, and I.-M. Lee Tetrahedron 64 2008 7178 7182.
10. D.-H. Lee, Y.H. Lee, J.M. Harrowfield, I.-M. Lee, H.I. Lee, W.T. Lim, Y. Kim, and M.-J. Jin Tetrahedron 65 2009 1630 1634.
11. C. Agami, F. Couty, and G. Evano Tetrahedron: Asymmetry 13 2002 297 302.
12. F. Couty, G. Evano, and N. Rabasso Tetrahedron: Asymmetry 14 2003 2407 2412.
13. F. Couty, and D. Prim Tetrahedron: Asymmetry 13 2002 2619 2624.
14. C. Agami, F. Couty, and N. Rabasso Tetrahedron Lett. 43 2002 4633 4636.
15. M. Sivaprakasam, F. Couty, O. David, J. Marrot, R. Sridhar, B. Srinivas, and K.R. Rao Eur. J. Org. Chem. 34 2007 5734 5739.
16. F. Hosono, S. Nishiyama, S. Yamamura, T. Izawa, and K. Kato Bioorg. Med. Chem. Lett. 4 1994 2083 2086.
17. V. Kurteva Modern aspects of azetidine synthesis T. Kaufman, E. Larghi, Modern Approaches to the Synthesis of O- and N-Heterocycles Vol. 3 2007 Research Signpost Kerala, India 45 71.
18. A. Brandi, S. Cicchi, and F.M. Cordero Chem. Rev. 108 2008 3988 4035.
19. F. Couty, G. Evano, and D. Prim Minirev. Org. Chem. 1 2004 133 148.
20. F. Faigl, A. Thurner, M. Battancs, F. Farkas, L. Poppe, V. Bódai, I. Kmecz, and B. Simándi Tetrahedron: Asymmetry 16 2005 3841 3847.
21. A. Thurner, F. Faigl, L. Tke, A. Mordini, M. Valacchi, G. Reginato, and G. Czira Tetrahedron 57 2001 8173 8180.
22. A. Mordini, S. Bindi, S. Pecchi, A. Degl'Innocenti, G. Reginato, and A. Serci J. Org. Chem. 61 1996 4374 4378.
23. F. Faigl, A. Thurner, F. Farkas, M. Battancs, and L. Poppe Chirality 19 2007 197 202.
24. A. Mordini, S. Pecchi, G. Capozzi, A. Capperucei, A. Degl'Innocenti, G. Reginato, and A. Ricci J. Org. Chem. 59 1994 4784 4790.
25. M. Schlosser Pure Appl. Chem. 60 1988 1627 1634.
26. CrystalClear SM 1.4.0 (Rigaku/MSC Inc., 2008).
27. G.M. Sheldrick Acta Cryst. A64 2008 112 122.